Reaction of Carbohydrate Halides with Magnesium. Novel C-C Coupling of Sugar Derivatives via Organometallic Intermediates

Article abstract of DOI:10.1021/jo00338a029

The reaction of 3-deoxy-3-C-(iodomethyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (1c) with sublimed magnesium in refluxing tetrahydrofuran gave dimer 2 and only traces of the 3-deoxy-3-methyl derivative 1d.Similarly methyl 5-deoxy-5-iodo-2,3-O-isopro